Alkyl esters of l-ascorbic acid: Stability, surface behaviour and interaction with phospholipid monolayers

Mottola, Milagro; Vico, Raquel V.; Villanueva, Martín Eduardo; Fanani, María Laura

doi:10.1016/j.jcis.2015.07.014

Cited by 35 publications

(51 citation statements)

References 42 publications

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“…The addition of ASCn, reaching a 1:1 drug:lipid molar ratio, induced restructuration of the particles, changing their size distribution. The drug concentration chosen for this study (100 M) represents several folds the critical aggregation concentration of ASC12 (33 M), ASC14 (9 M) and ASC16 (8 M) [20]. It is well established that the monomeric form of the amphiphile is the responsible for its interaction with the membrane [21].…”

Section: Ascn Induce Reorganization Of Popc Vesiclesmentioning

confidence: 99%

“…The aim of the present work is to delve in the understanding of the consequences of ASCn incorporation into lipid bilayers by exposing phospholipid vesicles, used as a biomembrane model system, to the non-commercial compounds ASC14 and ASC12 (synthesized in our laboratory [10]) and comparing their effect to that observed for the commercial ASC16.…”

Section: _ Introductionmentioning

confidence: 99%

“…We also explored the occurrence of condensed drug-enriched domains laterally segregated from the phospholipid rich phase, as has been shown to occur in analogues monolayer systems [10,11].…”

Section: _ Introductionmentioning

confidence: 99%

“…We recently studied the surface behavior of ASCn with acyl chains of different lengths, showing that these type of drugs have high surface activity where they are able to form stable Gibbs monolayers and were also capable to penetrate into tightly-packed phospholipid monolayers [10]. Subtle chemical differences in these compounds (which contain acyl chains of C16, C14 and C12) have large implications on the surface activity and upon the in-plane organization of the ASCn films as well as in their ability to be integrated into lipid monolayers [10][11][12][13]. We also demonstrated that these differences induce differential changes of the physicochemical properties of the targeted lipid membrane and regulate the extent of drug incorporation and the kinetics of the penetration process [12].…”

mentioning

confidence: 99%

“…Subtle chemical differences in these compounds (which contain acyl chains of C16, C14 and C12) have large implications on the surface activity and upon the in-plane organization of the ASCn films as well as in their ability to be integrated into lipid monolayers [10][11][12][13]. We also demonstrated that these differences induce differential changes of the physicochemical properties of the targeted lipid membrane and regulate the extent of drug incorporation and the kinetics of the penetration process [12].The aim of the present work is to delve in the understanding of the consequences of ASCn incorporation into lipid bilayers by exposing phospholipid vesicles, used as a biomembrane model system, to the non-commercial compounds ASC14 and ASC12 (synthesized in our laboratory [10]) and comparing their effect to that observed for the commercial ASC16.Here, we used PC nano and micro-size liposomes as model lipid membranes and we show that ASCn alter the structural integrity of those vesicles as well as the rheological properties of the phospholipid membrane. We also explored the occurrence of condensed drug-enriched domains laterally segregated from the phospholipid rich phase, as has been shown to occur in analogues monolayer systems [10,11].…”

mentioning

confidence: 99%

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The amphiphilic alkyl ester derivatives of l -ascorbic acid induce reorganization of phospholipid vesicles

Giudice

Ambroggio

Mottola

et al. 2016

Biochimica et Biophysica Acta (BBA) - Biomembranes

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l-ascorbic acid alkyl esters (ASCn) are lipophilic forms of vitamin C, which maintain some of its antioxidant power. Those properties make this drug family attractive to be used in pharmacological preparations protecting other redox-sensible drugs or designed to reduce possible toxic oxidative processes. In this work, we tested the ability of l-ascorbic acid alkyl esters (ASCn) to modulate the structure, permeability, and rheological properties of phospholipid bilayers. The ASCn studied here (ASC16, ASC14, and ASC12) alter the structural integrity as well as the rheological properties of phospholipid membranes without showing any evident detergent activity. ASC14 appeared as the most efficient drug in destabilize the membrane structure of nano- and micro-size phospholipid liposomes inducing vesicle content leakage and shape elongation on giant unilamellar vesicles. It also was the most potent enhancer of membrane microviscosity and surface water structuring. Only ASC16 induced the formation of drug-enriched condensed domains after its incorporation into the lipid bilayer, while ASC12 appeared as the less membrane-disturbing compound, likely because of its poor, and more superficial, partition into the membrane. We also found that incorporation of ASCn into the lipid bilayers enhanced the reduction of membrane components, compared with soluble vitamin C. Our study shows that ASCn compounds, which vary in the length of the acyl chain, show different effects on phospholipid vesicles used as biomembrane models. Those variances may account for subtly differences in the effectiveness on their pharmacological applications.

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Section: Ascn Induce Reorganization Of Popc Vesiclesmentioning

confidence: 99%

Section: _ Introductionmentioning

confidence: 99%

Section: _ Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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The amphiphilic alkyl ester derivatives of l -ascorbic acid induce reorganization of phospholipid vesicles

Giudice

Ambroggio

Mottola

et al. 2016

Biochimica et Biophysica Acta (BBA) - Biomembranes

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Structure of Ascorbyl Palmitate Bilayers (Aspasomes) from Molecular Dynamics Simulation

Han

2018

Bulletin Korean Chem Soc

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Renewable Surfactants for Biochemical Applications and Nanotechnology

Guenic

Chaveriat

Lequart

et al. 2018

J Surfact & Detergents

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Surfactants find applications in almost every chemical industry, such as household and industrial cleaning, paper, inks, agrochemicals, and personal care or pharmaceuticals. However, their production and use can have a negative impact on the environment and health. Increasing environmental concerns and the strong interest in renewable resources have led to the development of innovative and environmentally friendly surfactants produced by clean and/or sustainable technologies. The aim of this review is to explore the different types of surfactants and their architectures. Then, it will describe the two categories of renewable surfactants: biosurfactants obtained by fermentation, and bio‐based surfactants containing either a bio‐sourced polar head group or a bio‐sourced hydrophobic tail. Finally, this review will focus on highly specialized applications of surfactants (protein crystallization, transfection, and nanotechnology), which are closely related to the ability of surfactants to organize themselves in supramolecular architectures.

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Alkyl esters of l-ascorbic acid: Stability, surface behaviour and interaction with phospholipid monolayers

Cited by 35 publications

References 42 publications

The amphiphilic alkyl ester derivatives of l -ascorbic acid induce reorganization of phospholipid vesicles

The amphiphilic alkyl ester derivatives of l -ascorbic acid induce reorganization of phospholipid vesicles

Structure of Ascorbyl Palmitate Bilayers (Aspasomes) from Molecular Dynamics Simulation

Renewable Surfactants for Biochemical Applications and Nanotechnology

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